Aromatic compound and organic electroluminescence device including the same

ABSTRACT

An aromatic compound which improves emission efficiency and an organic electroluminescence device including the same are provided. The organic electroluminescence device includes: a first electrode; a second electrode opposite to the first electrode; and a plurality of organic layers between the first electrode and the second electrode, where at least one organic layer among the plurality of organic layers includes the aromatic compound. The aromatic compound is represented by Formula 1 below.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation of U.S. patent application Ser. No.15/958,642, filed on Apr. 20, 2018, which claims priority to and thebenefit of Korean Patent Application No. 10-2017-0122057, filed in theKorean Intellectual Property Office on Sep. 21, 2017, the entirecontents of both of which are incorporated herein by reference.

BACKGROUND

Recently, the development of an organic electroluminescence displaydevice as an image display device is being actively conducted. Differentfrom a liquid crystal display device, the organic electroluminescencedisplay device is a so-called self-luminescent display device in whichholes and electrons injected from a first electrode and a secondelectrode recombine in an emission layer, and a luminescent materialincluding an organic compound in the emission layer emits light todisplay an image.

An organic electroluminescence device includes, for example, a firstelectrode, a hole transport layer disposed on the first electrode, anemission layer disposed on the hole transport layer, an electrontransport layer disposed on the emission layer, and a second electrodedisposed on the electron transport layer. Holes are injected from thefirst electrode, and the injected holes move via the hole transportlayer and are injected to the emission layer. Meanwhile, electrons areinjected from the second electrode, and the injected electrons move viathe electron transport layer and are injected to the emission layer. Theholes and electrons injected to the emission layer recombine to generateexcitons in the emission layer. The organic electroluminescence deviceemits light that is generated by the radiation deactivation of theexcitons. In addition, the organic electroluminescence device is notlimited to the above-described configuration, but various suitablemodifications may be possible.

In the application of an organic electroluminescence device to a displaydevice, the decrease of the driving voltage, and the increase of theemission efficiency and the life of the organic electroluminescencedevice are required, and developments on materials for an organicelectroluminescence device attaining the requirements stably are beingcontinuously pursued.

SUMMARY

An aspect according to embodiments of the present disclosure is directedtoward an aromatic compound for an organic electroluminescence devicehaving a high efficiency.

Another aspect according to embodiments of the present disclosure isdirected toward an organic electroluminescence device including anaromatic compound in an organic layer and having a high efficiency andlong life.

According to an embodiment of the inventive concept, an aromaticcompound is represented by the following Formula 1:

In Formula 1, R₁ to R₃ may be each independently represented by Formula2 below, or a hydrogen atom, where at least one of R₁ to R₃ may berepresented by Formula 2.

In Formula 1, X may be O or S.

In Formula 2, Y₁ to Y₃ may be each independently CH or N.

In Formula 2, L may be a direct linkage, a substituted or unsubstitutedarylene group having 6 to 12 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 5 to 11 carbonatoms for forming a ring.

In Formula 2, Ar₁ and Ar₂ may be each independently represented byFormula 3 or Formula 4, or a hydrogen atom, where at least one of Ar₁ orAr₂ may be represented by Formula 3 or Formula 4:

In Formula 3 and Formula 4, Z₁ to Z₃ may be each independently CR₅ or N.

In Formula 3 and Formula 4, Z₄ may be O or S; R₄ may be a hydrogen atom,a cyano group, or a substituted or unsubstituted silyl group; and R₅ maybe a hydrogen atom, or a substituted or unsubstituted aryl group.

In an embodiment, the aromatic compound represented by Formula 1 may berepresented by the following Formula 1-1 or Formula 1-2:

In Formula 1-1 and Formula 1-2, X, L, Y₁ to Y₃, Ar₁, and Ar₂ are thesame as respectively defined in Formulae 1 and 2.

In an embodiment, a moiety represented by Formula 2 may be representedby one of the following Formula 2-1 to Formula 2-4:

In Formula 2-1 to Formula 2-4, L, Y₁ to Y₃, Z₁ to Z₄, and R₄ are thesame as respectively defined in Formulae 2 to 4.

In an embodiment, a moiety represented by Formula 3 may be representedby one of the following Formula 3-1 to Formula 3-7:

In an embodiment, a moiety represented by Formula 4 may be representedby the following Formula 4-1 or 4-2

In an embodiment, L may be a direct linkage, a substituted orunsubstituted phenylene group, a substituted or unsubstituted divalentbiphenyl group, or a substituted or unsubstituted heteroarylene groupcontaining N as a heteroatom.

In an embodiment, L may be represented by one of the following FormulaL-1 to Formula L-7:

In an embodiment, the aromatic compound represented by Formula 1 may beone selected from the compounds represented in the following CompoundGroup 1:

According to an embodiment of the inventive concept, an organicelectroluminescence device includes a first electrode, a secondelectrode opposite to the first electrode, and a plurality of organiclayers between the first electrode and the second electrode, wherein atleast one organic layer among the plurality of organic layers includesan aromatic compound represented by the following Formula 1:

In Formula 1, R₁ to R₃ may be each independently represented by Formula2 below, or a hydrogen atom, where at least one of R₁ to R₃ may berepresented by Formula 2 below.

In Formula 1, X may be O or S.

In Formula 2, Y₁ to Y₃ may be each independently CH or N.

In Formula 2, L may be a direct linkage, a substituted or unsubstitutedarylene group having 6 to 12 carbon atoms for forming a ring, or asubstituted or unsubstituted heteroarylene group having 5 to 11 carbonatoms for forming a ring.

In Formula 2, Ar₁ and Ar₂ may be each independently represented by thefollowing Formula 3 or Formula 4, or a hydrogen atom, where at least oneof Ar₁ or Ar₂ may be represented by Formula 3 or Formula 4:

In Formula 3 and Formula 4, Z₁ to Z₃ may be each independently CR₅ or N.

In Formula 3 and Formula 4, Z₄ may be O or S; R₄ may be a hydrogen atom,a cyano group, or a substituted or unsubstituted silyl group; and R₅ maybe a hydrogen atom, or a substituted or unsubstituted aryl group.

In an embodiment, the plurality of organic layers may include a holetransport region on the first electrode, an emission layer on the holetransport region, and an electron transport region on the emissionlayer, wherein the emission layer includes the aromatic compoundrepresented by Formula 1.

In an embodiment, the emission layer may be a fluorescence emissionlayer including a first host and a first dopant, and the first host mayinclude the aromatic compound represented by Formula 1.

In an embodiment, the emission layer may be a phosphorescence emissionlayer including a second host and a second dopant, and the second hostmay include the aromatic compound represented by Formula 1.

In an embodiment, the electron transport region may include the aromaticcompound represented by Formula 1.

In an embodiment, the emission layer may emit blue light.

In an embodiment, at least one organic layer among the plurality oforganic layers may include at least one selected from the aromaticcompounds represented in the following Compound Group 1:

BRIEF DESCRIPTION OF THE FIGURES

The accompanying drawings are included to provide a furtherunderstanding of the inventive concept, and are incorporated in andconstitute a part of this specification. The drawings illustrateexemplary embodiments of the inventive concept and, together with thedescription, serve to explain principles of the inventive concept. Inthe drawings:

FIG. 1 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment; and

FIG. 2 is a cross-sectional view schematically illustrating an organicelectroluminescence device according to an embodiment.

DETAILED DESCRIPTION

The inventive concept may have various modifications and may be embodiedin different forms, and example embodiments will be explained in moredetail with reference to the accompany drawings. The inventive conceptmay, however, be embodied in different forms and should not be construedas limited to the embodiments set forth herein. Rather, allmodifications, equivalents, and substituents which are included in thespirit and technical scope of the inventive concept should be includedin the inventive concept.

Like reference numerals refer to like elements throughout. In thedrawings, the dimensions of structures may be exaggerated for clarity ofillustration. It will be understood that, although the terms first,second, etc., may be used herein to describe various elements, theseelements should not be limited by these terms. These terms are only usedto distinguish one element from another element. Thus, a first elementcould be termed a second element without departing from the teachings ofthe present invention. Similarly, a second element could be termed afirst element. As used herein, the singular forms are intended toinclude the plural forms as well, unless the context clearly indicatesotherwise.

It will be understood that the terms “comprises” and/or “comprising,”when used in this specification, specify the presence of statedfeatures, numerals, steps, operations, elements, parts, or thecombination thereof, but do not preclude the presence or addition of oneor more other features, numerals, steps, operations, elements, parts, orthe combination thereof. It will also be understood that when a layer, afilm, a region, a plate, etc., is referred to as being “on” anotherpart, it can be “directly on” the other part, or intervening layers mayalso be present.

In the description, “

” represents a connecting site.

In the description, the term “substituted or unsubstituted” correspondsto (e.g., a functional group that is) substituted or unsubstituted withat least one substituent selected from a deuterium atom, a halogen atom,a nitro group, an amino group, a silyl group, a boron group, a phosphineoxide group, a phosphine sulfide group, an alkyl group, an alkenylgroup, an aryl group, and a heterocyclic group. In addition, each of thesubstituents may be substituted or unsubstituted. For example, abiphenyl group may be interpreted as an aryl group or a phenyl groupsubstituted with a phenyl group.

In the description, the terms “forming a ring via the combination withan adjacent group” may refer to forming a substituted or unsubstitutedhydrocarbon ring, or a substituted or unsubstituted heterocycle via thecombination with an adjacent group. The hydrocarbon ring includes analiphatic hydrocarbon ring and an aromatic hydrocarbon ring. Theheterocycle includes an aliphatic heterocycle and an aromaticheterocycle. The hydrocarbon ring and the heterocycle may be monocyclicor polycyclic. In addition, the ring formed via the combination with anadjacent group may be combined with another ring to form a spirostructure.

In the description, the terms “an adjacent group” may refer to asubstituent substituted for an atom which is directly combined with anatom substituted with a corresponding substituent, another substituentsubstituted for an atom which is substituted with a correspondingsubstituent, or a substituent sterically positioned at the nearestposition to a corresponding substituent. For example, in1,2-dimethylbenzene, two methyl groups may be interpreted as “adjacentgroups” to each other, and in 1,1-diethylcyclopentene, two ethyl groupsmay be interpreted as “adjacent groups” to each other.

In the description, the halogen atom may include a fluorine atom, achlorine atom, a bromine atom and an iodine atom.

In the description, the alkyl group may be a linear, branched or cyclicgroup. The carbon number of the alkyl group may be from 1 to 50, from 1to 30, from 1 to 20, from 1 to 10, or from 1 to 6. Non-limiting examplesof the alkyl group may include methyl, ethyl, n-propyl, isopropyl,n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl,n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl,3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl,1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl,4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl,2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl,2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl,n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl,2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl,2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, c-pentadecyl,n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl,2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl,2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl,n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl,n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

In the description, the aryl group refers to a (e.g., an optional)functional group or a substituent derived from an aromatic hydrocarbonring. The aryl group may be a monocyclic aryl group or a polycyclic arylgroup. The carbon number for forming a ring in the aryl group may be 6to 30, 6 to 20, or 6 to 15. Non-limiting examples of the aryl group mayinclude phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl,terphenyl, quaterphenyl, quinqphenyl, sexiphenyl, triphenylene, pyrenyl,benzofluoranthenyl, chrysenyl, etc.

In the description, the fluorenyl group may be substituted, and twosubstituents may combine to each other to form a spiro structure.

In the description, the heteroaryl group may be a heteroaryl groupincluding at least one of O, N, P, Si or S as a heteroatom. The carbonnumber for forming a ring of the heteroaryl group may be 2 to 30, or 2to 20. Examples of the heteroaryl group may include monocyclicheteroaryl group or polycyclic heteroaryl group. Examples of thepolycyclic heteroaryl group may have a dicyclic or tricyclic structure.Non-limiting examples of the heteroaryl group may include thiophene,furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole,pyridyl, bipyridyl, pyrimidyl, triazine, triazole, acridyl, pyridazine,pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phenoxazyl,phthalazinyl, pyrido pyrimidinyl, pyrido pyrazinyl, pyrazino pyrazinyl,isoquinoline, indole, carbazole, N-arylcarbazole, N-heteroarylcarbazole,N-alkylcarbazole, benzoxazole, benzoimidazole, benzothiazole,benzocarbazole, benzothiophene, dibenzothiophene, thienothiophene,benzofuranyl, phenanthroline, thiazolyl, isooxazolyl, oxadiazolyl,thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilole,dibenzofuranyl, etc.

In the description, explanation on the aryl group may be applied to thearylene group except that the arylene group is a divalent group.

In the description, explanation on the heteroaryl group may be appliedto the heteroarylene group except that the heteroarylene group is adivalent group.

Hereinafter, an aromatic compound according to an embodiment will beexplained.

An aromatic compound of an embodiment is represented by the followingFormula-1:

In Formula 1, R₁ to R₃ may be each independently represented by Formula2 below, or a hydrogen atom, where at least one of R₁ to R₃ may berepresented by Formula 2 below.

X may be O or S.

In Formula 1, R₁ may be represented by Formula 2, and R₂ and R₃ may beeach independently a hydrogen atom. In addition, R₃ may be representedby Formula 2, and R₁ and R₂ may be each independently a hydrogen atom.

In Formula 2, Y₁ to Y₃ may be each independently CH or N.

For example, Formula 2 may be a phenyl derivative if all of Y₁ to Y₃ areCH, may be a pyridine derivative if one of Y₁ to Y₃ is N and theremainder is CH, may be a pyrimidine derivative if two of Y₁ to Y₃ are Nand the remainder is CH, or may be a triazine derivative if all of Y₁ toY₃ are N.

L may be a direct linkage, a substituted or unsubstituted arylene grouphaving 6 to 12 carbon atoms for forming a ring, or a substituted orunsubstituted heteroarylene group having 5 to 11 carbon atoms forforming a ring. For example, L may be a substituted or unsubstitutedphenylene group. For example, L may be an unsubstituted phenylene group.

Ar₁ and Ar₂ may be each independently represented by the followingFormula 3 or Formula 4, or a hydrogen atom, where at least one of Ar₁and Ar₂ may be represented by the following Formula 3 or Formula 4:

In Formula 3 and Formula 4, Z₁ to Z₃ may be each independently CR₅ or N.For example, all of Z₁ to Z₃ may be CR₅, or at least one of Z₁ to Z₃ maybe N.

Z₄ may be O or S.

R₄ may be a hydrogen atom, a cyano group, or a substituted orunsubstituted silyl group.

R₅ may be a hydrogen atom, or a substituted or unsubstituted aryl group.

For example, R₄ may be an unsubstituted triphenylsilyl group, and R₅ maybe an unsubstituted phenyl group.

In Formula 1, R₁ may be a substituent represented by Formula 2, and R₂and R₃ may be each independently a hydrogen atom. In addition, inFormula 1, R₃ may be a substituent represented by Formula 2, and R₁ andR₂ may be each independently a hydrogen atom.

In one embodiment, the aromatic compound represented by Formula 1 may berepresented by the following Formula 1-1 or Formula 1-2:

In Formula 1-1 and Formula 1-2, descriptions of X, L, Y₁ to Y₃, Ar₁ andAr₂ are the same as respectively described in association with Formula 1and Formula 2 above.

Formula 1-1 represents an aromatic compound represented by Formula 1where R₁ is represented by Formula 2, and Formula 1-2 represents anaromatic compound represented by Formula 1 where R₃ is represented byFormula 2. In Formula 1-1 and Formula 1-2, Y₁ to Y₃ are eachindependently CH or N, and Ar₁ and Ar₂ are each independentlyrepresented by Formula 3 or Formula 4, or a hydrogen atom, where atleast one of Ar₁ and Ar₂ may be represented by Formula 3 or Formula 4.

Meanwhile, a moiety (e.g., the at least one of R₁ to R₃) represented byFormula 2 may be represented by one of the following Formula 2-1 toFormula 2-4:

Formula 2-1 represents a moiety of Formula 2 where Ar₁ and Ar₂ are eachindependently represented by Formula 3, Formula 2-2 represents a moietyof Formula 2 where Ar₁ is represented by Formula 3 and Ar₂ isrepresented by Formula 4, Formula 2-3 represents a moiety of Formula 2where Ar₁ and Ar₂ are each independently represented by Formula 4, andFormula 2-4 represents a moiety of Formula 2 where Ar₁ is represented byFormula 4 and Ar₂ is a hydrogen atom.

In Formula 2-1 to Formula 2-4, Z₁ to Z₃ may be each independently CR₅ orN; Z₄ may be O or S; R₄ may be a hydrogen atom, a cyano group, or asubstituted or unsubstituted silyl group. For example, R₄ may be atriphenylsilyl group. R₅ may be a hydrogen atom, or a substituted orunsubstituted aryl group. For example, R₅ may be a substituted orunsubstituted phenyl group. For example, R₅ may be an unsubstitutedphenyl group.

In Formula 2, L may be a direct linkage, a substituted or unsubstitutedphenylene group, a substituted or unsubstituted divalent biphenyl group,or a substituted or unsubstituted heteroarylene group containing N as aheteroatom.

For example, L may be represented by any one of the following L-1 toL-7:

Meanwhile, a moiety (e.g., the at least one of Ar₁ or Ar₂) representedby Formula may be represented by one of the following Formula 3-1 toFormula 3-7:

A moiety (e.g., the at least one of Ar₁ or Ar₂) represented by Formula 4may be represented by the following Formula 4-1 or 4-2:

In one embodiment, the aromatic compound represented by Formula 1 may beone selected from the compounds represented in the following CompoundGroup 1, but an embodiment of the inventive concept is not limitedthereto:

The above-described aromatic compound of an embodiment may be utilizedas a material for an organic electroluminescence device to improve theemission efficiency of the organic electroluminescence device. Thearomatic compound of an embodiment may have a high lowest tripletexcitation energy (T1). Since the aromatic compound of an embodiment hasa high lowest triplet excitation energy, the diffusion of tripletexcitons generated in an emission layer to a hole transport region maybe restrained, and the emission efficiency of an organicelectroluminescence device may be improved.

The aromatic compound of an embodiment may be utilized as a material ofan emission layer of an organic electroluminescence device to improvethe emission efficiency and external quantum efficiency of the organicelectroluminescence device.

Hereinafter, an organic electroluminescence device according to anembodiment of the inventive concept will be explained. Hereinafter,description of the above-described aromatic compound according to anembodiment of the inventive concept will not be repeated, andunexplained parts will follow the above explanation on the aromaticcompound according to an embodiment of the inventive concept.

FIG. 1 and FIG. 2 are cross-sectional views schematically illustratingan organic electroluminescence device according to an embodiment of theinventive concept. Referring to FIGS. 1 and 2 , an organicelectroluminescence device 10 according to an embodiment may include afirst electrode EL1, a hole transport region HTR, an emission layer EML,an electron transport region ETR, and a second electrode EL2 laminatedone by one. Meanwhile, when compared to FIG. 1 , FIG. 2 illustrates across-sectional view of an organic electroluminescence device of anembodiment, in which a hole transport region HTR includes a holeinjection layer HIL and a hole transport layer HTL, and an electrontransport region ETR includes an electron injection layer EIL and anelectron transport layer ETL.

The first electrode EL1 and the second electrode EL2 are oppositelydisposed to each other, and a plurality of organic layers may bedisposed between the first electrode EL1 and the second electrode EL2.The plurality of the organic layers may include the hole transportregion HTR, the emission layer EML, and the electron transport regionETR.

The organic electroluminescence device 10 of an embodiment may includethe aromatic compound of an embodiment in the emission layer EML.

In the explanation on an organic electroluminescence device 10 below, acase of including an aromatic compound of an embodiment in an emissionlayer EML will be explained in more detail. However, an embodiment ofthe inventive concept is not limited thereto. The aromatic compound ofan embodiment may be included in at least one of the plurality oforganic layers disposed between the first electrode EL1 and the secondelectrode EL2. For example, the aromatic compound according to anembodiment of the inventive concept may be included in the electrontransport region ETR.

The first electrode EL1 has conductivity. The first electrode EL1 may beformed utilizing a metal alloy or a conductive compound. The firstelectrode EL1 may be an anode.

The first electrode EL1 may be a transmissive electrode, a transflectiveelectrode, or a reflective electrode. If the first electrode EL1 is thetransmissive electrode, the first electrode EL1 may be formed utilizinga transparent metal oxide such as indium tin oxide (ITO), indium zincoxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). If thefirst electrode EL1 is the transflective electrode or the reflectiveelectrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd,Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, a compound thereof,or a mixture thereof (for example, a mixture of Ag and Mg). Also, thefirst electrode EL1 may include a plurality of layers including areflective layer, or a transflective layer formed utilizing the abovematerials, and a transmissive layer formed utilizing ITO, IZO, ZnO, orITZO. For example, the first electrode EL1 may include a plurality oflayers of ITO/Ag/ITO.

The hole transport region HTR is provided on the first electrode EL1.The hole transport region HTR may include at least one of a holeinjection layer HIL, a hole transport layer HTL, a hole buffer layer, oran electron blocking layer. The thickness of the hole transport regionHTR may be, for example, from about 1,000 Å to about 1,500 Å.

The hole transport region HTR may be a single layer formed utilizing asingle material, a single layer formed utilizing a plurality ofdifferent materials, or may have a multilayer structure including aplurality of layers formed utilizing a plurality of different materials.

For example, the hole transport region HTR may have the structure of asingle layer such as a hole injection layer HIL, or a hole transportlayer HTL, or may have a structure of a single layer formed utilizing ahole injection material and a hole transport material. Alternatively,the hole transport region HTR may have a structure of a single layerformed utilizing a plurality of different materials, or a structure ofhole injection layer HIL/hole transport layer HTL, hole injection layerHIL/hole transport layer HTL/hole buffer layer, hole injection layerHIL/hole buffer layer, hole transport layer HTL/hole buffer layer, orhole injection layer HIL/hole transport layer HTL/electron blockinglayer EBL, stacked from the first electrode in the stated order, withoutbeing limited thereto.

The hole transport region HTR may be formed utilizing various suitablemethods such as a vacuum deposition method, a spin coating method, acast method, a Langmuir-Blodgett (LB) method, an inkjet printing method,a laser printing method, and a laser induced thermal imaging (LITI)method.

If the hole transport region HTR includes the hole transport layer HTL,the hole transport region HTR may include any suitable hole transportmaterial available in the art. For example, the hole transport regionHTR may include 1,1-bis[(di-4-trileamino)phenyl]cyclohexane (TAPC),carbazole derivatives (such as N-phenyl carbazole and polyvinylcarbazole),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),N,N′-di(1-naphtyl)-N,N′-diphenylbenzidine (NPB), etc. However, anembodiment of the inventive concept is not limited thereto.

If the hole transport region HTR includes the hole injection layer HIL,the hole transport region HTR may include any suitable hole injectionmaterial available in the art. For example, the hole transport regionHTR may include triphenylamine-containing polyetherketone (TPAPEK),4-isopropyl-4′-methyldiphenyliodoniumtetrakis(pentafluorophenyl)borate(PPBI),N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-phenyl-4,4′-diamine(DNTPD), a phthalocyanine compound (such as copper phthalocyanine),4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB),4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris(N,N-2-naphthyphenylamino)-triphenylamine (2-TNATA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA), orpolyaniline/poly(4-styrenesulfonate) (PANI/PSS). However, an embodimentof the inventive concept is not limited thereto.

The thickness of the hole transport region HTR may be from about 100 Åto about 10,000 Å, for example, from about 100 Å to about 1,000 Å. Ifthe hole transport region HTR includes both the hole injection layer HILand the hole transport layer HTL, the thickness of the hole injectionlayer HIL may be from about 100 Å to about 10,000 Å, for example, fromabout 100 Å to about 1,000 Å, and the thickness of the hole transportlayer HTL may be from about 30 Å to about 1,000 Å. If the thicknesses ofthe hole transport region HTR, the hole injection layer HIL, and thehole transport layer HTL satisfy the above-described ranges,satisfactory hole transport properties may be obtained withoutsubstantial increase of a driving voltage.

The hole transport region HTR may further include a charge generatingmaterial in addition to the above-described materials to improveconductivity. The charge generating material may be dispersed uniformlyor non-uniformly in the hole transport region HTR. The charge generatingmaterial may be, for example, a p-dopant. Non-limiting examples of thep-dopant may be one of a quinone derivative, a metal oxide, or a cyanogroup-containing compound. For example, non-limiting examples of thep-dopant may include quinone derivatives (such astetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-tetracyanoquinodimethane (F4-TCNQ)), and a metaloxide (such as tungsten oxide and molybdenum oxide).

As described above, the hole transport region HTR may further include atleast one of a hole buffer layer or an electron blocking layer inaddition to the hole transport layer HTL and the hole injection layerHTL. The hole buffer layer may compensate a resonance distance accordingto the wavelength of light emitted from the emission layer EML andincrease light emission efficiency. Materials included in the holetransport region HTR may be utilized as materials included in the holebuffer layer. The electron blocking layer EBL is a layer reducing orpreventing electron injection from the electron transport region ETR tothe hole transport region HTR.

For example, the hole transport region HTR may include a hole injectionlayer HIL, a hole transport layer HTL and an electron blocking layer EBLin an embodiment.

The emission layer EML is provided on the hole transport region HTR. Thethickness of the emission layer EML may be from about 100 Å to about 600Å. The emission layer EML may be a single layer formed utilizing asingle material, a single layer formed utilizing a plurality ofdifferent materials, or may have a multilayer structure having aplurality of layers formed utilizing a plurality of different materials.

The emission layer EML may include the aromatic compound according to anembodiment of the inventive concept. For example, the emission layer EMLmay include the aromatic compound represented by Formula 1 and may emitphosphorescence or fluorescence.

In Formula 1, R₁ to R₃ may be each independently represented by Formula2 below, or a hydrogen atom, where at least one of R₁ to R₃ may berepresented by Formula 2 below.

In Formula 2, Y₁ to Y₃ may be each independently CH or N.

L may be a direct linkage, a substituted or unsubstituted arylene grouphaving 6 to 12 carbon atoms for forming a ring, or a substituted orunsubstituted heteroarylene group having 5 to 11 carbon atoms forforming a ring.

Ar₁ and Ar₂ may be each independently represented by the followingFormula 3 or Formula 4, or a hydrogen atom, where at least one of Ar₁and Ar₂ may be represented by the following Formula 3 or Formula 4:

In Formula 3 and Formula 4, Z₁ to Z₃ may be each independently CR₅ or N.

Z₄ may be O or S.

R₄ may be a hydrogen atom, a cyano group, or a substituted orunsubstituted silyl group.

R₅ may be a hydrogen atom, or a substituted or unsubstituted aryl group.

In Formula 1 to Formula 4, R₁ to R₅, X, Y₁ to Y₃, L, Ar₁, Ar₂, and Z₁ toZ₄ are the same as respectively described above in association with thearomatic compound of an embodiment.

An aromatic compound represented by Formula 1 has a high lowest tripletexcitation energy (T1). For example, the aromatic compound representedby Formula 1 may have the lowest triplet excitation energy (T1) of about3.2 eV or more.

The emission layer EML may include at least one of the compoundsrepresented in the following Compound Group 1:

The organic electroluminescence device 10 of an embodiment includes thearomatic compound of an embodiment represented by Formula 1 in anemission layer EML and may have improved emission efficiency. Inaddition, the organic electroluminescence device 10 of an embodimentincludes the aromatic compound of an embodiment represented by Formula 1in an emission layer EML and may have improved external quantumefficiency.

The emission layer EML may emit one of red light, green light, bluelight, white light, yellow light, or cyan light. For example, theemission layer EML may emit blue light in an organic electroluminescencedevice of an embodiment.

The emission layer EML may include a fluorescent material or aphosphorescent material. In addition, the emission layer EML may includea host and/or a dopant. In addition, the emission layer EML may have athickness of, for example, about 100 Å to about 600 Å.

In an embodiment, the emission layer EML may be a fluorescence emissionlayer. The emission layer EML of the organic electroluminescence device10 of an embodiment may be a delayed fluorescence emission layer. Theemission layer EML emitting fluorescence may include a first host and afirst dopant.

The aromatic compound of an embodiment represented by Formula 1 may beutilized as a host material of an emission layer EML emittingfluorescence. In an embodiment, the emission layer EML may be afluorescence emission layer, and the emission layer EML may include thearomatic compound of an embodiment and any suitable phosphorescentdopant available in the art. For example, the aromatic compoundaccording to an embodiment may be included as a host material of theemission layer EML.

Meanwhile, in an embodiment, the emission layer EML may include, as adopant, styryl derivatives (for example,1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB),4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), andN-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi)), perylene and the derivatives thereof (for example,2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and the derivativesthereof (for example, 1,1-dipyrene, 1,4-dipyrenylbenzene,1,4-bis(N,N-diphenylamino)pyrene), etc.

The aromatic compound according to an embodiment of the inventiveconcept may be included as a dopant material of an emission layer EML.For example, the aromatic compound of an embodiment may be utilized as adopant material which emits fluorescence. In an embodiment, the emissionlayer EML may be a fluorescence emission layer, and the emission layerEML may include any suitable host material available in the art and thearomatic compound of an embodiment. For example, the aromatic compoundof an embodiment may be included as a dopant material of an emissionlayer EML.

Meanwhile, the emission layer EML may include any suitable host materialavailable in the art in an embodiment. The host material may be anysuitable material available in the art without specific limitation andmay include, for example, tris(8-hydroxyquinolino)aluminum (Alq₃),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), poly(N-vinylcarbazole)(PVK), 9,10-di(naphthaline-2-yl)anthracene (ADN),4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi),3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2),hexaphenylcyclotrisiloxane (DPSiO₃), octaphenylcyclotetra siloxane(DPSiO₄), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), etc.

In an embodiment, the emission layer EML may be a phosphorescenceemission layer. The emission layer EML emitting phosphorescence mayinclude a second host which is a phosphorescent host and a second dopantwhich is a phosphorescent dopant.

In an embodiment, the emission layer EML may include the aromaticcompound of an embodiment as the second host. The aromatic compoundrepresented by Formula 1 may be utilized as a phosphorescent host of theemission layer EML, and the emission layer EML may further include asuitable (e.g., known) phosphorescent dopant material. In addition, inan embodiment, the emission layer EML may further include any suitablehost material available in the art together with the aromatic compoundrepresented by Formula 1.

The emission layer EML may include the aromatic compound of anembodiment and any suitable phosphorescent dopant available in the artmaterial. For example, the phosphorescent dopant may utilize a metalcomplex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), or thulium (Tm). For example, iridium(III)bis(4,6-difluorophenylpyridinato-N,C2′)picolinate (Flrpic),bis(2,4-difluorophenylpyridinato (Fir6), or platinum octaethyl porphyrin(PtOEP) may be utilized as a phosphorescent dopant. However, anembodiment of the inventive concept is not limited thereto.

Meanwhile, the emission layer EML may further include any suitablephosphorescent host material available in the art, for example,bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS).

If the emission layer EML emits red light, the emission layer EML mayinclude, for example, tris(dibenzoylmethanato)phenanthroline europium(PBD:Eu(DBM)₃(Phen)), or a phosphorescent material including perylene.If the emission layer EML emits red light, the dopant included in theemission layer EML may be selected from a metal complex or anorganometallic complex (such as bis(1-phenylisoquinoline)acetylacetonateiridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetonate iridium(PQr(acac)), tris(1-phenylquinoline)iridium (PQIr), andoctaethylporphyrin platinum (PtOEP)), rubrene and the derivativesthereof, or4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) andthe derivatives thereof.

If the emission layer EML emits green light, the emission layer EML mayfurther include a phosphorescent material including, for example,tris(8-hydroxyquinolino)aluminum (Alq₃). If the emission layer EML emitsgreen light, the dopant included in the emission layer EML may beselected from a metal complex or an organometallic complex (such asfac-tris(2-phenylpyridine)iridium (Ir(ppy)3)), or a coumarin and thederivatives thereof.

If the emission layer EML emits blue light, the emission layer EML mayfurther include a phosphorescent material including at least oneselected from, for example, spiro-DPVBi, spiro-6P, distyryl-benzene(DSB), distyryl-arylene (DSA), a polyfluorene (PFO)-based polymer, and apoly(p-phenylene vinylene) (PPV)-based polymer. If the emission layerEML emits blue light, the dopant included in the emission layer EML maybe selected from a metal complex or an organometallic complex (such as(4,6-F2ppy)₂Irpic), or perylene and the derivatives thereof.

The electron transport region ETR is provided on the emission layer EML.The electron transport region ETR may include at least one of a holeblocking layer, an electron transport layer ETL or an electron injectionlayer EIL. However, an embodiment of the inventive concept is notlimited thereto.

The electron transport region ETR may be a single layer formed utilizinga single material, a single layer formed utilizing a plurality ofdifferent materials, or may have a multilayer structure having aplurality of layers formed utilizing a plurality of different materials.

For example, the electron transport region ETR may have a single layerstructure of the electron injection layer EIL or the electron transportlayer ETL, or a single layer structure formed utilizing an electroninjection material and an electron transport material. In addition, theelectron transport region ETR may have a single layer structure having aplurality of different materials, or a structure of electron transportlayer ETL/electron injection layer EIL, or hole blocking layer/electrontransport layer ETL/electron injection layer EIL, stacked from the firstelectrode EL1 in the stated order, without being limited thereto. Thethickness of the electron transport region ETR may be, for example, fromabout 1,000 Å to about 1,500 Å.

The electron transport region ETR may be formed utilizing varioussuitable methods such as a vacuum deposition method, a spin coatingmethod, a cast method, a Langmuir-Blodgett (LB) method, an inkjetprinting method, a laser printing method, and a laser induced thermalimaging (LITI) method.

If the electron transport region ETR includes the electron transportlayer ETL, the electron transport region ETR may include any suitablematerial available in the art. For example, the electron transportregion ETR may include tris(8-hydroxyquinolinato)aluminum (Alq₃),1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene,2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine,2-(4-(N-phenylbenzimidazolyl-1-ylphenyl)-9,10-dinaphthylanthracene,1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi),2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq), berylliumbis(benzoquinolin-10-olate (Bebq2),9,10-di(naphthalene-2-yl)anthracene (ADN), or a mixture thereof, withoutbeing limited thereto.

If the electron transport region ETR includes the electron transportlayer ETL, the thickness of the electron transport layer ETL may be fromabout 100 Å to about 1,000 Å and may be, for example, from about 150 Åto about 500 Å. If the thickness of the electron transport layer ETLsatisfies the above-described range, satisfactory electron transportproperties may be obtained without substantial increase of a drivingvoltage.

If the electron transport region ETR includes the electron injectionlayer EIL, the electron transport region ETR may include any suitablematerial available in the art. For example, the electron transportregion ETR may include LiF, lithium quinolate (LiQ), Li₂O, BaO, NaCl,CsF, a metal in lanthanoids (such as Yb), or a metal halide (such asRbCl, and RbI). However, an embodiment of the inventive concept is notlimited thereto. The electron injection layer EIL may also be formedutilizing a mixture material of an electron transport material and aninsulating organo metal salt. The organo metal salt may be a materialhaving an energy band gap of about 4 eV or more. The organo metal saltmay include, for example, metal acetates, metal benzoates, metalacetoacetates, metal acetylacetonates, or metal stearates.

If the electron transport region ETR includes the electron injectionlayer EIL, the thickness of the electron injection layer EIL may be fromabout 1 Å to about 100 Å, for example, from about 3 Å to about 90 Å. Ifthe thickness of the electron injection layer EIL satisfies the abovedescribed ranges, satisfactory electron injection properties may beobtained without inducing the substantial increase of a driving voltage.

The electron transport region ETR may include a hole blocking layer, asdescribed above. The hole blocking layer may include, for example, atleast one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), or4,7-diphenyl-1,10-phenanthroline (Bphen). However, an embodiment of theinventive concept is not limited thereto.

The second electrode EL2 is provided on the electron transport regionETR. The second electrode EL2 has conductivity. The second electrode EL2may be formed utilizing a metal alloy or a conductive compound. Thesecond electrode EL2 may be a cathode. The second electrode EL2 may be atransmissive electrode, a transflective electrode or a reflectiveelectrode. If the second electrode EL2 is the transmissive electrode,the second electrode EL2 may include a transparent metal oxide, forexample, ITO, IZO, ZnO, ITZO, etc.

If the second electrode EL2 is the transflective electrode or thereflective electrode, the second electrode EL2 may include Ag, Mg, Cu,Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, acompound thereof, or a mixture thereof (for example, a mixture of Ag andMg). Alternatively, the second electrode EL2 may have a multilayeredstructure including a reflective layer or a transflective layer formedutilizing the above-described materials and a transparent conductivelayer formed utilizing ITO, IZO, ZnO, ITZO, etc.

The second electrode EL2 may be coupled or connected with an auxiliaryelectrode. If the second electrode EL2 is coupled or connected with theauxiliary electrode, the resistance of the second electrode EL2 maydecrease.

In the organic electroluminescence device 10, according to theapplication of a voltage to each of the first electrode EL1 and secondelectrode EL2, holes injected from the first electrode EL1 may move viathe hole transport region HTR to the emission layer EML, and electronsinjected from the second electrode EL2 may move via the electrontransport region ETR to the emission layer EML. The electrons and theholes are recombined in the emission layer EML to produce excitons, andthe excitons may emit light via transition from an excited state to aground state.

If the organic electroluminescence device 10 is atop emission device,the first electrode EL1 may be a reflective electrode, and the secondelectrode EL2 may be a transmissive electrode or a transflectiveelectrode. If the organic electroluminescence device 10 is a bottomemission device, the first electrode EL1 may be a transmissive electrodeor a transflective electrode, and the second electrode EL2 may be areflective electrode.

An organic electroluminescence device of an embodiment includes thearomatic compound of an embodiment and may have improved emissionefficiency. In addition, the organic electroluminescence device of anembodiment includes the aromatic compound having a high lowest tripletenergy according to an embodiment in a hole transport region, and thediffusion of triplet excitons generated in an emission layer may berestrained and high external quantum efficiency may be achieved.

Meanwhile, the organic electroluminescence device of an embodiment maybe a blue emitting device, a green emitting device, a red emittingdevice or a white emitting device. In addition, if the organicelectroluminescence device of an embodiment is a blue emitting device,high emission efficiency may be achieved. However, an embodiment of theinventive concept is not limited thereto.

Hereinafter an aromatic compound of an embodiment and an organicelectroluminescence device including the aromatic compound of anembodiment will be explained in more detail with reference toembodiments and comparative embodiments. The following embodiments areonly illustrations to assist the understanding of the inventive concept,and the scope of the inventive concept is not limited thereto.

EXAMPLES 1. Synthesis of Aromatic Compounds

First, a synthetic method of the aromatic compounds according toexemplary embodiments will be explained referring to synthetic methodsof Compound 2, Compound 5, Compound 8, Compound 18, Compound 29,Compound 33 and Compound 43 in Compound Group 1. In addition, thefollowing synthetic methods of the aromatic compounds are forillustrations, and the synthetic method of the aromatic compoundaccording to an embodiment of the inventive concept is not limited tothe following examples.

Synthesis of Compound 2

Synthesis of Intermediate 2-1

As illustrated in Reaction 1, diphenyl ether was dissolved in THF andreacted with tetramethyl ethylenediamine (TMEDA) and nBuLi, and thenreacted with dichlorodiphenylsilane to obtain Intermediate 2-1.Intermediate 2-1 was identified by LC-MS. C₂₄H₁₈OSi: M+1 351.3

Synthesis of Intermediate 2-2

As illustrated in Reaction 1, Intermediate 2-1 was dissolved in THF, andreacted with TMEDA and nBuLi, and then reacted with trimethyl borate toobtain Intermediate 2-2. Intermediate 2-2 was identified by LC-MS.C₂₄H₁₉BO₃Si: M+1 395.2.

Synthesis of Compound 2

As illustrated in Reaction 1, 3.4 g of 2-chloro-4,6-diphenyltriazine(CAS No.=3842-55-5), 6.0 g of Intermediate 2-2, 0.58 g oftetrakis(triphenylphosphine)palladium, and 4.3 g of potassium carbonatewere injected into a reactor, and dissolved in 80 ml of toluene, 20 mlof ethanol and 20 ml of distilled water, followed by refluxing for about24 hours. After finishing the reaction, the reaction solution wasextracted with ethyl acetate, and a collected organic layer was driedwith magnesium sulfate. Solvents were evaporated, and the residue thusobtained was separated by silica gel column chromatography to obtain 4.9g (yield: 67%) of Compound 2. Compound 2 was identified by MS/FAB and¹H-NMR, and the results are shown in Table 1 below.

Synthesis of Compound 5

Synthesis of Intermediate 5-1

As illustrated in Reaction 2, bis(2-bromophenyl)sulfide was dissolved inTHF and reacted with nBuLi, and then reacted with dichlorodiphenylsilaneto obtain Intermediate 5-1. Intermediate 5-1 was identified by LC-MS.C₂₄H₁₈SSi: M+1 367.2

Synthesis of Intermediate 5-2

As illustrated in Reaction 2, Intermediate 5-1 was dissolved in THF, andreacted with TMEDA and nBuLi, and then reacted with trimethyl borate toobtain Intermediate 5-2. Intermediate 5-2 was identified by LC-MS.C₂₄H₁₉BO₂SSi: M+1 395.2.

Synthesis of Compound 5

As illustrated in Reaction 2, 2.1 g of2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (CAS No.=864377-31-1), 2.6g of Intermediate 5-2, 0.25 g of tetrakis(triphenylphosphine)palladium,and 1.9 g of potassium carbonate were injected into a reactor, anddissolved in 30 ml of toluene, 10 ml of ethanol and 10 ml of distilledwater, followed by refluxing for about 24 hours. After finishing thereaction, the reaction solution was extracted with ethyl acetate, and acollected organic layer was dried with magnesium sulfate. Solvents wereevaporated, and the residue thus obtained was separated by silica gelcolumn chromatography to obtain 2.8 g (yield: 77%) of Compound 5.Compound 5 was identified by MS/FAB and ¹H-NMR, and the results areshown in Table 1 below.

Synthesis of Compound 8

As illustrated in Reaction 3, 1.8 g of 2,4-dichloro-6-phenyltriazine(CAS No.=1700-02-3), 3.0 g of Intermediate 2-2, 0.33 g oftetrakis(triphenylphosphine)palladium, and 2.5 g of potassium carbonatewere injected into a reactor, and dissolved in 30 ml of toluene, 10 mlof ethanol and 10 ml of distilled water, followed by refluxing for about24 hours. After finishing the reaction, the reaction solution wasextracted with ethyl acetate, and a collected organic layer was driedwith magnesium sulfate. Solvents were evaporated, and the residue thusobtained was separated by silica gel column chromatography to obtain 3.4g (yield: 55%) of Compound 8. Compound 8 was identified by MS/FAB and¹H-NMR, and the results are shown in Table 1 below.

Synthesis of Compound 18

Synthesis of Intermediate 18-1

As illustrated in Reaction 4, Intermediate 2-2 was reacted with2,4-dichloro-6-phenyltriazine under the conditions of a Pd catalyst toobtain Intermediate 18-1. Intermediate 18-1 was identified by LC-MS.C₃₃H₂₂Cl₂N₂OSi: M+1 561.2.

Synthesis of Compound 18

As illustrated in Reaction 4, 1.2 g of 3-(triphenylsilyl)phenyl)boronicacid (CAS No.=1253912-58-1), 1.5 g of Intermediate 18-1, 0.12 g oftetrakis(triphenylphosphine)palladium, and 0.9 g of potassium carbonatewere injected into a reactor, and dissolved in 20 ml of toluene, 5 ml ofethanol and 5 ml of distilled water, followed by refluxing for about 24hours. After finishing the reaction, the reaction solution was extractedwith ethyl acetate, and a collected organic layer was dried withmagnesium sulfate. Solvents were evaporated, and the residue thusobtained was separated by silica gel column chromatography to obtain 1.6g (yield: 71%) of Compound 18. Compound 18 was identified by MS/FAB and1H-NMR, and the results are shown in Table 1 below.

Synthesis of Compound 29

Synthesis of Intermediate 29-1

As illustrated in Reaction 5, diphenyl ether was dissolved in THF andreacted with TMEDA and nBuLi, and then reacted with dichloro(4-chlorophenyl)(phenyl)silane to obtain Intermediate 29-1. Intermediate29-1 was identified by LC-MS. C₂₄H₁₇ClOSi: M+1 385.1

Synthesis of Intermediate 29-2

As illustrated in Reaction 5, Intermediate 29-1 andbis(pinacolato)diboron were reacted under the conditions of a Pdcatalyst to obtain Intermediate 29-2. Intermediate 29-2 was identifiedby LC-MS. C₃₀H₂₉BO₃Si: M+1 477.3.

Synthesis of Compound 29

As illustrated in Reaction 5, 4.7 g of Intermediate 29-2 and 2.2 g of2-chloro-4,6-diphenyltriazine (CAS No.=3842-55-5), 0.38 g oftetrakis(triphenylphosphine)palladium, and 2.8 g of potassium carbonatewere injected into a reactor, and dissolved in 40 ml of toluene, 10 mlof ethanol and 10 ml of distilled water, followed by refluxing for about24 hours. After finishing the reaction, the reaction solution wasextracted with ethyl acetate, and a collected organic layer was driedwith magnesium sulfate. Solvents were evaporated, and the residue thusobtained was separated by silica gel column chromatography to obtain 3.1g (yield: 65%) of Compound 29. Compound 29 was identified by MS/FAB and¹H-NMR, and the results are shown in Table 1 below.

Synthesis of Compound 33

Synthesis of Intermediate 33-1

As illustrated in Reaction 6,1,3-dibromo-5-(triphenylsilyl)benzene (CASNo.=1030856-97-3) and Intermediate 2-2 were reacted under the conditionsof a Pd catalyst to obtain Intermediate 33-1. Intermediate 33-1 wasidentified by LC-MS. C₄₈H₃₅BrOSi₂: M+1 763.2

Synthesis of Intermediate 33-2

As illustrated in Reaction 6, Intermediate 33-1 andbis(pinacolato)diboron were reacted under the conditions of a Pdcatalyst to obtain Intermediate 33-2. Intermediate 33-2 was identifiedby LC-MS. C₅₄H₄₇BO₃Si₂: M+1 811.2.

Synthesis of Compound 33

As illustrated in Reaction 6, 4.7 g of Intermediate 33-2 and 1.3 g of2-chloro-4,6-diphenylpyrimidine (CAS No.=2915-16-4), 0.22 g oftetrakis(triphenylphosphine)palladium, and 1.7 g of potassium carbonatewere injected into a reactor, and dissolved in 40 ml of toluene, 10 mlof ethanol and 10 ml of distilled water, followed by refluxing for about24 hours. After finishing the reaction, the reaction solution wasextracted with ethyl acetate, and a collected organic layer was driedwith magnesium sulfate. Solvents were evaporated, and the residue thusobtained was separated by silica gel column chromatography to obtain 2.5g (yield: 55%) of Compound 33. Compound 33 was identified by MS/FAB and¹H-NMR, and the results are shown in Table 1 below.

Synthesis of Compound 43

Synthesis of Intermediate 43-1

As illustrated in Reaction 7,2,4-dichloro-6-phenyltriazine and(2-cyanophenyl)boronic acid were reacted under the conditions of a Pdcatalyst to obtain Intermediate 43-1. Intermediate 43-1 was identifiedby LC-MS. C₁₆H₉ClN₄: M+1 293.1

Synthesis of Intermediate 43-2

As illustrated in Reaction 7, Intermediate 2-2 and 3-bromoiodobenzenewere reacted under the conditions of a Pd catalyst to obtainIntermediate 43-2. Intermediate 43-2 was identified by LC-MS.C₃₀H₂₁BrOSi: M+1 505.1.

Synthesis of Intermediate 43-3

As illustrated in Reaction 7, Intermediate 43-2 andbis(pinacolato)diboron were reacted under the conditions of a Pdcatalyst to obtain Intermediate 43-3. Intermediate 43-3 was identifiedby LC-MS. C₃₆H₃₃BO₃Si: M+1 553.1.

Synthesis of Compound 43

As illustrated in Reaction 7, 3.2 g of Intermediate 43-1 and 6.8 g ofIntermediate 43-3, 0.50 g of tetrakis(triphenylphosphine)palladium, and3.6 g of potassium carbonate were injected into a reactor, and dissolvedin 60 ml of toluene, 15 ml of ethanol and 15 ml of distilled water,followed by refluxing for about 24 hours. After finishing the reaction,the reaction solution was extracted with ethyl acetate, and a collectedorganic layer was dried with magnesium sulfate. Solvents wereevaporated, and the residue thus obtained was separated by silica gelcolumn chromatography to obtain 4.4 g (yield: 63%) of Compound 43.Compound 43 was identified by MS/FAB and ¹H-NMR, and the results areshown in Table 1 below.

TABLE 1 MS/FAB Measured Compound ¹H NMR (CDCl₃, 400 MHz) value [M + 1]Calc. 2 8.34 (d, 4H), 8.04 (d, 1H), 7.52-7.33 (m, 20H), 582.1 581.757.11 (d, 1H), 7.05 (t, 1H) 5 8.38-8.33 (m, 5H), 7.92 (s, 1H), 7.73-7.62674.1 673.20 (m, 3H), 7.50-7.45 (m, 11H), 7.37-7.32 (m, 10H), 7.11 (t,1H) 8 8.36 (d, 2H), 8.05 (d, 2H), 7.52-7.41 (m, 15H), 854.4 853.267.37-7.35 (m, 14H), 7.11-7.05 (m, 4H) 18 8.37-8.30 (m, 3H), 7.86 (s,1H), 7.63 (t, 1H), 840.2 839.28 7.52-7.36 (m, 32H), 7.11 (d, 1H), 7.07(t, 1H) 29 8.35 (d, 4H), 7.87 (m, 2H), 7.65 (m, 2H), 582.6 581.197.44-7.36 (m, 4H), 7.11-7.08 (m, 2H) 33 8.24 (s, 1H), 8.04-7.92 (m, 8H),7.52-7.33 915.4 914.31 (m, 35H), 7.12 (d, 1H), 7.08 (t, 1H) 43 8.37 (d,1H), 8.36 (m, 2H), 8.04 (d, 2H), 683.7 682.86 7.94-7.90 (m, 2H),7.78-7.70 (m, 4H), 7.61 (d, 1H), 7.52-7.36 (m, 17H), 7.11-7.08 (m, 2H)

2. Manufacture and Evaluation of Organic Electroluminescence DevicesIncluding Aromatic Compounds

An organic electroluminescence device including an aromatic compound ofan embodiment in an emission layer was manufactured as follows. Organicelectroluminescence devices of Examples 1 to 7 were manufacturedutilizing the aromatic compounds of Compound 2, Compound 5, Compound 8,Compound 18, Compound 29, Compound 33 and Compound 43 as emission layermaterials, respectively. Organic electroluminescence devices ofComparative Examples 1 to 4 were manufactured utilizing ComparativeCompounds C1 to C4 as emission layer materials, respectively.

Compounds utilized for forming emission layers of Examples 1 to 7 andComparative Examples 1 to 4 are shown in Table 2 below.

TABLE 2 Compound 2

Compound 5

Compound 8

Compound 18

Compound 29

Compound 33

Compound 43

Comparative Compound C1

Comparative Compound C2

Comparative Compound C3

Comparative Compound C4

The organic electroluminescence devices of the examples and thecomparative examples were manufactured as follows.

A first electrode was formed utilizing an ITO substrate having athickness of about 1,200 Å. The ITO substrate was prepared by cleaningutilizing ultrasonic waves with isopropyl alcohol and pure water forabout 5 minutes for each and then by exposing to ultraviolet light forabout 30 minutes and ozone. The ITO substrate thus cleansed wasinstalled in a vacuum deposition apparatus.

On the cleansed and prepared ITO substrate, a hole injection layer wasformed by depositing NPD in vacuum. The hole injection layer was formedto a thickness of about 300 Å. On the hole injection layer, mCP wasdeposited in vacuum to form a hole transport layer. The hole transportlayer was formed to a thickness of about 200 Å.

Then, an emission layer including the aromatic compound of an embodimentwas formed on the hole transport layer. The emission layer was formed byco-depositing the aromatic compound of an embodiment and a dopantmaterial, Ir(pmp)3 in a weight ratio of 92:8 to a thickness of about 250Å.

Then, on the emission layer,3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ) wasdeposited to a thickness of about 200 Å as an electron transport layer.After that, on the electron transport layer, LiF, which is an alkalimetal halide, was deposited to a thickness of about 10 Å to form anelectron injection layer. Then, Al was deposited to a thickness of about100 Å to form a second electrode. By forming a LiF/Al electrode, anorganic electroluminescence device was manufactured.

The materials utilized in the organic electroluminescence devices may berepresented by the following formulae:

Examples 1 to 7 utilize different (e.g., different kinds of) aromaticcompounds as the host materials of an emission layer. Meanwhile, in thecomparative examples, organic electroluminescence devices weremanufactured by substantially the same manufacturing method of theorganic electroluminescence devices of the examples except for utilizingComparative Compounds C1 to C4, respectively.

(Evaluation of Properties of Organic Electroluminescence Devices)

In order to evaluate the properties of the organic electroluminescencedevices according to the examples and the comparative example, a drivingvoltage at current density of 10 mA/cm², current density and maximumquantum efficiency were measured. The driving voltage and the currentdensity of the organic electroluminescence devices were measuredutilizing a source meter (Keithley Instrument Co., 2400 series), and themaximum quantum efficiency was measured utilizing an external quantumefficiency measurement apparatus C9920-2-12 of Hamamatsu Photonics Co.For the evaluation of the maximum quantum efficiency, luminance/currentdensity was measured utilizing luminescence system of which wavelengthsensitivity was calibrated, and converting into the maximum quantumefficiency supposing angle luminance distribution (Lambertian)introducing (e.g., assuming Lambertian angle luminance distribution and)perfect diffusion reflection surface. The evaluation results on theproperties of the organic electroluminescence devices are shown in Table3 below.

TABLE 3 Maximum Driving Current quantum Emis- Emission voltage densityefficiency sion Division layer (V) (mA/cm²) (%) color Example 1 Compound2 3.6 2.3 18.9 Blue Example 2 Compound 5 3.8 2.3 18.2 Blue Example 3Compound 8 4.1 2.3 17.3 Blue Example 4 Compound 18 4.5 2.3 20.2 BlueExample 5 Compound 29 3.9 2.3 21.3 Blue Example 6 Compound 33 4.1 2.319.1 Blue Example 7 Compound 43 4.3 2.3 21.5 Blue ComparativeComparative 5.5 2.3 12.4 Blue Example 1 Compound C1 ComparativeComparative 4.6 2.3 2.5 Blue Example 2 Compound C2 ComparativeComparative 5.6 2.3 15.5 Blue Example 3 Compound C3 ComparativeComparative 4.5 2.3 3.3 Blue Example 4 Compound C4

Referring to the results of Table 3, it was found that the organicelectroluminescence devices of Examples 1 to 7 have higher efficiencywhen compared to the organic electroluminescence devices of ComparativeExamples 1 to 4.

The organic electroluminescence device of an embodiment includes thearomatic compound of an embodiment in an emission layer and may achievehigh emission efficiency. The aromatic compound of an embodiment maydecrease the driving voltage of an organic electroluminescence deviceand improve blue emission efficiency. In addition, by appropriatelyintroducing a substituent in a compound represented by Formula 1 in theorganic electroluminescence device of an embodiment, blue emission maybe achieved, and concurrently (e.g., at the same time), high externalquantum efficiency may be achieved.

An aromatic compound of an embodiment may improve the life and emissionefficiency of an organic electroluminescence device.

An organic electroluminescence device of an embodiment includes anaromatic compound of an embodiment in an organic layer, for example, inan emission layer, and may achieve high efficiency and long life.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration. As used herein, the term “and/or”includes any and all combinations of one or more of the associatedlisted items. Expressions such as “at least one of,” when preceding alist of elements, modify the entire list of elements and do not modifythe individual elements of the list.

Also, any numerical range recited herein is intended to include allsubranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

Although the exemplary embodiments of the present invention have beendescribed, it is understood that the present invention should not belimited to these exemplary embodiments but various changes andmodifications can be made by one ordinary skilled in the art within thespirit and scope of the present invention as hereinafter claimed, andequivalents thereof.

What is claimed is:
 1. An aromatic compound represented by Formula 1:

wherein in Formula 1, R_(a) to R_(d) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₁ to R₃ are each independently represented by Formula 2, or a hydrogenatom, wherein at least one of R₁ to R₃ is represented by Formula 2, X isO or S, n_(a), n_(c), and n_(d) are each independently an integer of 0to 4, and n_(b) is an integer of 0 to 3:

wherein in Formula 2, Y₁ to Y₃ are each independently CR₄ or N, L is adirect linkage, a substituted or unsubstituted arylene group having 6 to12 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 5 to 11 carbon atoms for forming a ring, R₄is a hydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30ring-forming carbon atoms, Ar₁ and Ar₂ are each independently a hydrogenatom, a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring-forming carbon atoms, or represented byFormula 4, wherein at least one of Ar₁ or Ar₂ is a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, asubstituted or unsubstituted pyridine group, a substituted orunsubstituted pyrimidine group, or represented by Formula 4:

wherein in Formula 4, R_(e) to R_(h) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₅ to R₇ are each independently a position to be connected to Formula 2,or a hydrogen atom, wherein at least one of R₅ to R₇ is a position to beconnected to Formula 2, Z₄ is O or S, n_(e), n_(g), and n_(h) are eachindependently an integer of 0 to 4, and n_(f) is an integer of 0 to 3.2. The aromatic compound of claim 1, wherein R_(a) to R_(d) are eachindependently a hydrogen atom.
 3. The aromatic compound of claim 1,wherein R_(e) to R_(h) are each independently a hydrogen atom.
 4. Thearomatic compound of claim 1, wherein L is a direct linkage, asubstituted or unsubstituted phenylene group, a substituted orunsubstituted divalent biphenyl group, or a substituted or unsubstitutedheteroarylene group containing N as a heteroatom.
 5. The aromaticcompound of claim 1, wherein the aromatic compound represented byFormula 1 is represented by Formula 1-1 or Formula 1-2:

wherein in Formula 1-1 and Formula 1-2, X, L, Y₁ to Y₃, Ar₁, Ar₂, R_(a)to R_(d), n_(a) to n_(d) are the same as respectively defined inFormulae 1 and
 2. 6. The aromatic compound of claim 1, wherein a moietyrepresented by Formula 4 is represented by Formula 4-1:

wherein in Formula 4, —* is a position to be connected to Formula 2, Z₄,R_(e) to R_(h), n_(e) to n_(h) are the same as respectively defined inFormula
 4. 7. The aromatic compound of claim 1, wherein the aromaticcompound represented by Formula 1 is one selected from compoundsrepresented in Compound Group 1:


8. An aromatic compound represented by Formula 1:

wherein in Formula 1, R_(a) to R_(d) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₁ to R₃ are each independently represented by Formula 2, or a hydrogenatom, wherein at least one of R₁ to R₃ is represented by Formula 2, X isO or S, n_(a), n_(c), and n_(d) are each independently an integer of 0to 4, and n_(b) is an integer of 0 to 3:

wherein in Formula 2, Y₁ to Y₃ are each independently CR₄ or N, L is adirect linkage, a substituted or unsubstituted arylene group having 6 to12 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 5 to 11 carbon atoms for forming a ring, R₄is a hydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30ring-forming carbon atoms, Ar₁ and Ar₂ are each independently asubstituted or unsubstituted phenyl group, a substituted orunsubstituted pyridine group, a substituted or unsubstituted pyrimidinegroup, or represented by Formula 4:

wherein in Formula 4, R_(e) to R_(h) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₅ to R₇ are each independently a position to be connected to Formula 2,or a hydrogen atom, wherein at least one of R₅ to R₇ is a position to beconnected to Formula 2, Z₄ is O or S, n_(e), n_(g), and n_(h) are eachindependently an integer of 0 to 4, and n_(f) is an integer of 0 to 3.9. An organic electroluminescence device, comprising: a first electrode;a second electrode opposite to the first electrode; and a plurality oforganic layers between the first electrode and the second electrode,wherein at least one organic layer from among the plurality of organiclayers comprises an aromatic compound represented by Formula 1:

wherein in Formula 1, R_(a) to R_(d) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₁ to R₃ are each independently represented by Formula 2, or a hydrogenatom, wherein at least one of R₁ to R₃ is represented by Formula 2, X isO or S, n_(a), n_(c), and n_(d) are each independently an integer of 0to 4, and n_(b) is an integer of 0 to 3:

wherein in Formula 2, Y₁ to Y₃ are each independently CR₄ or N, L is adirect linkage, a substituted or unsubstituted arylene group having 6 to12 carbon atoms for forming a ring, or a substituted or unsubstitutedheteroarylene group having 5 to 11 carbon atoms for forming a ring, R₄is a hydrogen atom, a deuterium atom, a halogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30ring-forming carbon atoms, Ar₁ and Ar₂ are each independently a hydrogenatom, a substituted or unsubstituted aryl group having 6 to 30ring-forming carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring-forming carbon atoms, or represented byFormula 4, wherein at least one of Ar₁ or Ar₂ is a substituted orunsubstituted aryl group having 6 to 30 ring-forming carbon atoms, asubstituted or unsubstituted pyridine group, a substituted orunsubstituted pyrimidine group, or represented by Formula 4:

wherein in Formula 4, R_(e) to R_(h) are each independently a hydrogenatom, a deuterium atom, a halogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a substituted or unsubstitutedaryl group having 6 to 30 ring-forming carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms,R₅ to R₇ are each independently a position to be connected to Formula 2,or a hydrogen atom, wherein at least one of R₅ to R₇ is a position to beconnected to Formula 2, Z₄ is O or S, n_(e), n_(g), and n_(h) are eachindependently an integer of 0 to 4, and n_(f) is an integer of 0 to 3.